Not many teen comedies from the mid-1990s have stood the test of time, or even been remembered. Amy Heckerling’s Clueless is an exception. 25 years on since its original release, the film seems just as relevant, relatable, and entertaining as it was back in 1995. Based loosely on the Jane Austen novel Emma, it is the story of Beverly Hills socialite Cher Horowitz (Alicia Silverstone) who can’t help but get involved in the love lives of those around her. With the arrival of new girl, Tai (Brittany Murphy), on the scene, Cher and her BFF Dionne (Stacey Dash) are greeted with a new challenge, to make-over regular-looking Tai and transform her into the most popular girl in school. What follows of course, is much hilarity as Tai finds herself a fish out of water,  and all sorts of drama revolving around various boys, including a very young Paul Rudd.

Clueless was originally conceived as a TV movie. In 1993, Heckerling was developing a TV show called No Worries which focused on the life of popular kids attending a California high school. The idea of what eventually became Clueless came about after Heckerling’s No Worries script was rejected by Disney for being, “too smart”, Heckerling’s intention being to create a smart narrative with a typical ‘dumb blonde’ character at the centre of the film.

Heckerling had been toying with the idea of Clueless ever since reading Austen’s Emma, and says, “I’ve always loved [Emma] and part of it had sort of stored it away in my brain… So I really related to her and got into it. And the plot was so brilliantly laid out in Emma. So I tried to take all the things that were in this sort of pretty 1800s world and see what would that be like if it was in Beverly Hills.”

The theatrical trailer for Clueless from 1995.

However, the network executives decided against bringing Heckerling’s show to pilot. The director was about to throw in the towel, when her agent told her not to despair, because he thought the idea could work as a movie, and actively began trying to line up a deal. Heckerling proposed the idea of Clueless the movie to the Fox studio executives. Fox were keen on the idea, but had a caveat: they wanted more male characters. As Heckerling discussed later in an interview withThe Baltimore Sun, “They were worried about something that was so female-oriented. They kept pressuring me to create more of a life for the boys in the film, to create more of an ensemble piece.”

The Fox studio executives had another prboem with Heckerling’s script, namely the relationship between Cher and her ex-stepbrother Josh (Rudd). However, as Heckerling explained to them, “They’re not related. Their parents were briefly married and [Cher’s] father is still nice to [Josh]. That’s not verboten, you know?” Still, Fox weren’t budging on their demands for more male characters, and this was the breaking point for Heckerling. She wanted to focus primarily on telling the story from a female perspective – still a relatively uncommon thing in the mid-1990s – and what the studio were proposing went against her entire vision for the movie, so she ultimately rejected it and walked away from the project.

It wasn’t until Scott Rudin (Oscar winning producer of the likes of No Country For Old Men, The Social Network and Lady Bird) got his hands on the script that things picked up again. Rudin thought the female-centric angle was an unique selling point and saw the script’s potential. He convinced Paramount to make Clueless without forcing Heckerling to add more male characters into the story. As Heckerling recounts during an interview with Vice, “I told Scott Rudin, ‘here are all the things I used to have in the film’, and he told me to put it all back.” Cher became the main character again, and the romantic relationship between Cher and Josh was re-introduced back into the story.

With Paramount and Rudin on board, Heckerling’s attention turned to casting. Nowadays, it’s hard to imagine anyone but Alicia Silverstone as Cher, but at first the studio wasn’t too keen on the seventeen-year-old. Actresses such as Gwyneth Paltrow, Tiffani Thiessen, Reese Witherspoon and Angelina Jolie all auditioned and were in talks for the role. However, Heckerling had seen Silverstone’s performance in the video for Aerosmth’s Cryin‘ and, believing Silverstone embodied everything that Heckerling imagined in Cher, she hired the young star-in-waiting. Paul Rudd, on the other hand, was so convinced that he hadn’t secured the role of Josh that he shaved off his hair, which prompted Heckerling to tell him off when she ran into him at an L.A. restaurant. 28 year old Stacey Dash was cast as Cher’s right hand girl, Dionne, (although Lauryn Hill also auditioned for the role). For the role of Tai, Alanna Ubach was very nearly cast but Brittany Murphy blew everyone away with her audition, with Heckerling commenting on her “naturally funny spirit”.

Production began in November 1994, with a 40-day filming schedule. Producers sat in on classes at Beverly Hills High School to get a feel for the student culture. Although on-screen the world of Clueless looks bright and sunny, shooting took place during an uncommonly wet winter, leading to frustrating problems for the crew. A real house had been rented for Cher’s home and massive amounts of rain left the garden a wet, muddy mess. As a result, the house’s floors ended up sustaining damage from people bringing in all sorts of debris from outside. Additionally, equipment trucks were parked near the Sepulveda basin, which started to flood due to several straight days of rain. This resulted in rangers coming to inform the production team that they needed to move or else risk being swept away.

Aside from these few minor issues, filming seemed to go reasonably well without any major incidents. Clueless opened in July 1995 and became a surprise hit, grossing a total of $56 million against a budget of $12 million. The film propelled Silverstone to stardom (though it wasn’t exactly long-lived) and, in 1996, the producers created a spin-off Clueless television series, which followed the continuing adventures of Cher and her friends. Several cast members from the film went on to star in the series, with the notable exceptions of Silverstone (replaced by Rachel Blanchard) and Rudd. Sadly, the ratings were so low that ABC cancelled the show after just one season. UPN picked it up for two seasons, only to cancel it for the exact same reason.

On its release, Clueless had an impact and influence on pop culture, with phrases like “As if” and “Totally Buggin’” part of teenage vernacular for a time in the 1990s. The film was also forward-thinking in terms of its representation of female friendship as well as being progressive with its depiction of a gay character on the big screen. The film has remained a part of the public consciousness with the likes of Iggy Azalea paying homage to the film in the music video for her 2014 song “Fancy”. In December 2018, a jukebox musical based on Clueless opened, written by Heckerling herself. It had a short run and closed in January 2019. There have been talks of Paramount Studios rebooting the film but we would most likely see this version of Clueless grace the small screen rather than be released in theatres. Regardless of whether or not we do get a Clueless remake, we can all take the time to appreciate the wit, originality, and progressiveness of of Amy Heckerling’s 1995 film.